3-Chloro-4-fluoroaniline → 2-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-cyano-3-fluoro-phenyl)-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

HRID 2204405Notes

Reaction equation

HRID 2204405 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=2)[N:7]([CH:20]([CH3:22])[CH3:21])[C:6]=1[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([F:33])[CH:26]=1)O)=[O:4].[NH2:34][C:35]1[CH:36]=[C:37]([Cl:43])[C:38](=[O:42])[N:39]([CH3:41])[CH:40]=1.C(OC(C1C=CN(C(C)C)C=1C(C1C=CC(C#N)=CC=1)O)=O)C.ClC1C=C(C=CC=1F)N>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([O:16][CH3:17])=[N:14][CH:15]=2)[N:7]([CH:20]([CH3:22])[CH3:21])[C:6]=1[CH:23]([NH:34][C:35]1[CH:36]=[C:37]([Cl:43])[C:38](=[O:42])[N:39]([CH3:41])[CH:40]=1)[C:25]1[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]([F:33])[CH:26]=1)=[O:4]

Participants

5

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneHCID 867031112-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 867032182-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867032172-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-cyano-3-fluoro-phenyl)-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Procedure

The title compound was prepared in analogy to the procedures described for Step H2 and Step H3 but 2-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-5-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step 195.2) and 5-amino-3-chloro-1-methyl-1H-pyridin-2-one (Step E5) were used instead of 2-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester and 3-chloro-4-fluoroaniline respectively. The title compound was obtained as a blue solid. tR: 1.10 min (HPLC 3); ESI-MS: tR=1.07 min, [M+H]+ 595/597 (LC-MS 1); TLC: Rf=0.29 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedures

Sources & evidence

ORD record
ord-422cb0358fe3412bbf76703090286ae4
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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